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CHEBI:17347 ChEBI 82579 ChemSpider Androgen and Estrogen Metabolism 937 ChemSpider HMDB00374 HMDB 19-HYDROXYTESTOSTERONE BioCyc 439153 PubChem-compound ReactionCatalysis946 ACTIVATION 1.0 ReactionCatalysis944 ACTIVATION ReactionCatalysis945 ACTIVATION ReactionCatalysis943 ACTIVATION HMDB00145 HMDB 6013 PubChem-compound Oxidized flavoprotein 3-oxo-5-alpha-steroid 4-dehydrogenase 1 NADPH C25H36O8 Testosterone glucuronide 464.24103 HMDB00142 HMDB CHEBI:17474 ChEBI 1.0 14808-79-8 CAS 1.0 PW000045 PathWhiz HMDB00234 HMDB Cytochrome P450 19A1 HMDB01448 HMDB CHEBI:17200 ChEBI 1.0 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider HMDB59597 HMDB Phosphoadenosine phosphosulfate C19H28O5S Dehydroepiandrosterone sulfate 368.16574 SubPathwayInteraction167 SubPathway167Reaction SubPathwayReaction C00468 KEGG Compound 12594 PubChem-compound UDP-GLUCURONATE BioCyc 6031 PubChem-compound 1010 ChemSpider HMDB00363 HMDB 1.0 8036443 ChemSpider 1.0 1.0 C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 HMDB01425 HMDB C02538 KEGG Compound HMDB00217 HMDB Testosterone CHEBI:17263 ChEBI C19H28O3 19-Hydroxytestosterone 304.20386 C19H30O2 5b-Dihydrotestosterone 290.22458 3001028 PubChem-compound CHEBI:5086 ChEBI Sulfotransferase family cytosolic 2B member 1 1.0 HMDB03959 HMDB 1180-25-2 CAS 17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O BioCyc HMDB00221 HMDB P08842 UniProt C00007 KEGG Compound C00006 KEGG Compound CHEBI:18009 ChEBI CHEBI:220467 ChEBI Dehydroepiandrosterone 50-28-2 CAS C00001 KEGG Compound Beta-D-Glucuronides BioCyc 1.0 P18405 UniProt C00005 KEGG Compound C00004 KEGG Compound SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O C00003 KEGG Compound CHEBI:16189 ChEBI NADP 1.0 Steryl-sulfatase UDP-glucuronosyltransferase 2B17 UDP-glucuronosyltransferase 2B11 Steroidogenesis SubPathway Oxygen Estrone sulfate C11134 KEGG Compound BiologicalState49 Cytochrome P450 19A1 C01227 KEGG Compound C21H28N7O14P2 NAD 664.11694 1.0 6128 PubChem-compound C00015 KEGG Compound 5660 ChemSpider NAD(P) BioCyc P37058 UniProt 10189 ChemSpider Dehydroepiandrosterone sulfate H Hydrogen Ion 1.007825 C19H24O3 19-Oxoandrost-4-ene-3,17-dione 300.17255 5898 ChemSpider HMDB03955 HMDB CHEBI:17252 ChEBI 6238 PubChem-compound O75310 UniProt 53-84-9 CAS O75795 UniProt 17a-Hydroxypregnenolone 1.0 17-beta-Estradiol-3-glucuronide 5b-Dihydrotestosterone 482-67-7 CAS 19-Hydroxyandrost-4-ene-3,17-dione P14060 UniProt SMP00130 SMPDB P14061 UniProt 1.14.14.14 false 1.14.14.14 19-Oxoandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → Estrone + Formic acid + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 19-Hydroxyandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → 19-Oxoandrost-4-ene-3,17-dione + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT CL:0000000 CELL TYPE ONTOLOGY 1.14.14.14 false 1.14.14.14 Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 Oxygen + Reduced flavoprotein + Testosterone → 19-Hydroxytestosterone + Oxidized flavoprotein + Water LEFT_TO_RIGHT Dihydrotestosterone 1.3.1.22 false 1.3.1.22 Dihydrotestosterone + NADP ↔ Hydrogen Ion + NADPH + Testosterone REVERSIBLE SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O SMILES C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O 17465008 ChemSpider 3-oxo-5-alpha-steroid 4-dehydrogenase 1 C00280 KEGG Compound 1.14.14.14 false 1.14.14.14 19-Oxotestosterone + Oxygen + Reduced flavoprotein → Estradiol + Formic acid + Oxidized flavoprotein LEFT_TO_RIGHT HMDB02961 HMDB 1.14.14.14 false 1.14.14.14 19-Hydroxytestosterone + Oxygen + Reduced flavoprotein → 19-Oxotestosterone + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT 1.1.1.62 false 1.1.1.62 Estradiol + NADP ↔ Estrone + NADPH REVERSIBLE 2.8.2.4 false 2.8.2.4 Estrone + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Estrone sulfate LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT C00167 KEGG Compound 108192 PubChem-compound 1.0 Estradiol 17-beta-dehydrogenase 1 17a-Hydroxypregnenolone SubPathwayOutput 12074 ChemSpider Testosterone 17-beta-dehydrogenase 3 C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 1.0 O00204 UniProt 3.1.6.2 false 3.1.6.2 Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Sulfate LEFT_TO_RIGHT C10H15N5O13P2S Phosphoadenosine phosphosulfate 506.98624 C05297 KEGG Compound 140102 ChemSpider CPD-352 BioCyc C05503 KEGG Compound 1.0 SMILES [O-]S([O-])(=O)=O C00054 KEGG Compound C00053 KEGG Compound 19-Hydroxyandrost-4-ene-3,17-dione 7732-18-5 CAS C00059 KEGG Compound C00058 KEGG Compound 1.0 19-Oxotestosterone 1.0 Water SMILES [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Estrogen sulfotransferase FORMATE BioCyc Oxidized flavoprotein 16522 ChemSpider Reaction24 false 17-Hydroxyprogesterone → Androstenedione LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Testosterone → Testosterone glucuronide LEFT_TO_RIGHT 68-96-2 CAS 1.3.1.3 false 1.3.1.3 5b-Dihydrotestosterone + NADP ↔ Hydrogen Ion + NADPH + Testosterone REVERSIBLE Estrogen sulfotransferase 1.0 C19H30O2 Dihydrotestosterone 290.22458 11302 PubChem-compound 10214 PubChem-compound Reaction21 false 17a-Hydroxypregnenolone → Dehydroepiandrosterone LEFT_TO_RIGHT BiologicalState18 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 1.0 1.0 1.0 1.0 962 PubChem-compound 58-98-0 CAS 1.0 Reduced flavoprotein 1.0 C04555 KEGG Compound Oxidized flavoprotein SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 Steroid 17-alpha-hydroxylase/17,20 lyase C00080 KEGG Compound SMILES O=O BiologicalState8 SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 5809 ChemSpider SMILES OC=O 1.0 1.0 Estradiol 17-beta-dehydrogenase 1 C01176 KEGG Compound 53-43-0 CAS Steryl-sulfatase Sulfotransferase family cytosolic 2B member 1 Testosterone 1.0 1.0 64-18-6 CAS 3-oxo-5-beta-steroid 4-dehydrogenase 16399653 PubChem-compound 22833512 PubChem-compound Androstenedione SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO UDP-glucuronosyltransferase 2B11 1.0 P49888 UniProt ReactionCatalysis929 ACTIVATION H2O Water 18.010565 1.0 Uridine 5'-diphosphate 18667985 ChemSpider NADH BioCyc Testosterone 17-beta-dehydrogenase 3 NAD BioCyc 977 PubChem-compound SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O Steroid 17-alpha-hydroxylase/17,20 lyase P51857 UniProt Formic acid UDP-glucuronosyltransferase 2B17 NAD Reduced flavoprotein 17215925 ChemSpider 97270 ChemSpider 2.0 O4S Sulfate 95.95173 19-Hydroxytestosterone SMILES O C19H28O2 Testosterone 288.20892 C21H30O3 17-Hydroxyprogesterone 330.21948 ReactionCatalysis27 ACTIVATION Cytochrome P450 19A1 2.8.2.2 false 2.8.2.2 Dehydroepiandrosterone + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfate LEFT_TO_RIGHT 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 2616-64-0 CAS ReactionCatalysis29 ACTIVATION C19H26O2 Androstenedione 286.19327 10635 PubChem-compound ReactionCatalysis20 ACTIVATION ReactionCatalysis24 ACTIVATION 6002 ChemSpider Reduced flavoprotein ReactionCatalysis22 ACTIVATION Uridine diphosphate glucuronic acid Water CHEBI:15846 ChEBI CHEBI:16814 ChEBI HMDB00935 HMDB C10H15N5O10P2 Adenosine 3',5'-diphosphate 427.02942 5870 PubChem-compound 53-59-8 CAS 10827 ChemSpider 651-48-9 CAS 1.0 ReactionCatalysis30 ACTIVATION 5757 PubChem-compound ESTRONE-SULFATE BioCyc 1038 PubChem-compound ReactionCatalysis34 ACTIVATION ReactionCatalysis35 ACTIVATION 16395893 PubChem-compound ReactionCatalysis32 ACTIVATION ReactionCatalysis33 ACTIVATION 17-Hydroxyprogesterone SubPathwayOutput 1.0 C24H32O8 17-beta-Estradiol-3-glucuronide 448.20972 278 ChemSpider C18H22O5S Estrone sulfate 350.1188 17461292 ChemSpider 13783824 PubChem-compound HMDB00902 HMDB CHEBI:16908 ChEBI ReactionCatalysis49 ACTIVATION Sulfate ReactionCatalysis47 ACTIVATION ReactionCatalysis48 ACTIVATION ReactionCatalysis46 ACTIVATION HMDB06224 HMDB 13628409 ChemSpider 221136 ChemSpider SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O HMDB03193 HMDB C21H30N7O17P3 NADPH 745.0911 3-5-ADP BioCyc C21H29N7O17P3 NADP 744.08325 C21H32O3 17a-Hydroxypregnenolone 332.23514 1.0 DEHYDRO-EPIANDROSTERONE-SULFATE BioCyc NADPH BioCyc 1053-73-2 CAS 1.0 CPD-6641 BioCyc ANDROST4ENE BioCyc 58-68-4 CAS 2126-37-6 CAS SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3 1.0 SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O C19H26O3 19-Hydroxyandrost-4-ene-3,17-dione 302.1882 1.0 1.0 510-64-5 CAS NADH Oxygen Androstenedione 1.0 Estrogen sulfotransferase C19H26O3 19-Oxotestosterone 302.1882 9799 ChemSpider 1.0 58-22-0 CAS C05138 KEGG Compound SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O SMILES [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C 1.0 SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O 159296 PubChem-compound 17473 PubChem-compound CHEBI:28835 ChEBI 91451 PubChem-compound Estrone Oxygen 53-57-6 CAS 17-Hydroxyprogesterone Reaction51 false Dehydroepiandrosterone + NAD → Androstenedione + Hydrogen Ion + NADH LEFT_TO_RIGHT HMDB06770 HMDB Reaction55 false 17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + Hydrogen Ion + NADH LEFT_TO_RIGHT C21H29N7O14P2 NADH 665.12476 1117 PubChem-compound 1.0 C19H28O2 Dehydroepiandrosterone 288.20892 1.0 571-22-2 CAS GO:0005737 GENE ONTOLOGY 1.0 Dehydroepiandrosterone CHEBI:17985 ChEBI 1.0 19-Oxoandrost-4-ene-3,17-dione Estradiol Endoplasmic Reticulum Endoplasmic Reticulum Membrane 1085 ChemSpider 4075-13-2 CAS NADH SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O C00951 KEGG Compound Androstenedione CHEBI:17980 ChEBI UDP BioCyc 5682 ChemSpider 521-18-6 CAS C05293 KEGG Compound C05295 KEGG Compound Reduced flavoprotein C05294 KEGG Compound C05290 KEGG Compound Dehydroepiandrosterone sulfate HMDB06769 HMDB CHEBI:16422 ChEBI HMDB06768 HMDB Estradiol SMILES [H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O 3-oxo-5-beta-steroid 4-dehydrogenase P05093 UniProt 5554 ChemSpider 5675 ChemSpider 5791 ChemSpider Water NAD 18971002 PubChem-compound Cytoplasm NADPH CHEBI:28750 ChEBI CHEBI:428206 ChEBI Cell NH42SO4 BioCyc 12850019 PubChem-compound 1.0 ESTRONE BioCyc CHEBI:36489 ChEBI 2.0 388299 ChemSpider 1.0 HMDB00077 HMDB C18H22O2 Estrone 270.162 Hydrogen Ion O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 9860744 PubChem-compound 19-Hydroxytestosterone GO:0005789 GENE ONTOLOGY C18H24O2 Estradiol 272.17764 GO:0005783 GENE ONTOLOGY 7782-44-7 CAS SMILES [H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C 9606 TAXONOMY 1.0 53-16-7 CAS 1.0 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O CHEBI:16330 ChEBI PW000141 PathWhiz HMDB00295 HMDB HMDB00053 HMDB 5893 PubChem-compound HMDB02111 HMDB PAPS BioCyc 1.0 CHEBI:30751 ChEBI SMP00068 SMPDB Oxidized flavoprotein CHEBI:15377 ChEBI Cytochrome P450 19A1 CHEBI:15379 ChEBI C03917 KEGG Compound CHEBI:15378 ChEBI SMILES [H+] CHEBI:16469 ChEBI SMILES CC12CCC3C(CCC4CC(=O)CCC34C)C1CCC2O 2272513 ChemSpider HMDB00061 HMDB 5886 PubChem-compound Adenosine 3',5'-diphosphate HMDB01032 HMDB 1.0 1.0 19-OXO-TESTOSTERONE BioCyc 387-79-1 CAS 481-97-0 CAS HMDB01487 HMDB C00535 KEGG Compound 1.0 HMDB00151 HMDB SMILES [H]C12CC[C@H](O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C SMILES O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O CHEBI:27576 ChEBI 1.0 63-05-8 CAS NADP HMDB01377 HMDB HMDB01134 HMDB P11511 UniProt CHEBI:17659 ChEBI 1.1.1.64 false 1.1.1.64 NAD + Testosterone → Androstenedione + Hydrogen Ion + NADH LEFT_TO_RIGHT CHEBI:1069535 ChEBI 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 252379 PubChem-compound Testosterone glucuronide Estrogen sulfotransferase Estradiol 17-beta- dehydrogenase 1 UDP- glucuronosyltransferase 2B11 Cytochrome P450 19A1 Steroid 17-alpha- hydroxylase/17,20 lyase 3-beta-HSD 1 Steroid 17-alpha- hydroxylase/17,20 lyase 3-beta-HSD 1 Sulfotransferase family cytosolic 2B member 1 Cytochrome P450 19A1 Testosterone 17-beta- dehydrogenase 3 3-oxo-5-beta- steroid 4-dehydrogenase 3-oxo-5- alpha-steroid 4-dehydrogenase 1 UDP- glucuronosyltransferase 2B17 Steryl- sulfatase 17-Hydroxyprogesterone 17a-Hydroxypregnenolone Estrone Phosphoadenosine phosphosulfate Estrone sulfate Adenosine 3',5'-diphosphate 19-Oxoandrost-4-ene-3,17-dione Estradiol NADP NADPH 19-Oxotestosterone 19-Hydroxyandrost-4-ene- 3,17-dione 19-Hydroxytestosterone Uridine diphosphate glucuronic acid 17-beta-Estradiol-3- glucuronide Uridine 5'-diphosphate Androstenedione O 2 H 2 O NAD NADH Dehydroepiandrosterone NAD NADH Phosphoadenosine phosphosulfate Adenosine 3',5'-diphosphate Dehydroepiandrosterone sulfate Testosterone O 2 H 2 O NAD NADH H + 5b-Dihydrotestosterone Dihydrotestosterone NADP NADPH H + Testosterone glucuronide H 2 O Sulfate Heme Heme Heme Heme Calcium Reduced flavoprotein Oxidized flavoprotein Steroidogenesis ER Membrane ER Membrane Cytoplasm ER Lumen ER Lumen Smooth Endoplasmic Reticulum Intracellular Space Extracellular Space
CHEBI:17347 ChEBI 82579 ChemSpider Androgen and Estrogen Metabolism 937 ChemSpider HMDB00374 HMDB 19-HYDROXYTESTOSTERONE BioCyc 439153 PubChem-compound ReactionCatalysis946 ACTIVATION 1.0 ReactionCatalysis944 ACTIVATION ReactionCatalysis945 ACTIVATION ReactionCatalysis943 ACTIVATION HMDB00145 HMDB 6013 PubChem-compound Oxidized flavoprotein 3-oxo-5-alpha-steroid 4-dehydrogenase 1 NADPH C25H36O8 Testosterone glucuronide 464.24103 HMDB00142 HMDB CHEBI:17474 ChEBI 1.0 14808-79-8 CAS 1.0 PW000045 PathWhiz HMDB00234 HMDB Cytochrome P450 19A1 HMDB01448 HMDB CHEBI:17200 ChEBI 1.0 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider HMDB59597 HMDB Phosphoadenosine phosphosulfate C19H28O5S Dehydroepiandrosterone sulfate 368.16574 SubPathwayInteraction167 SubPathway167Reaction SubPathwayReaction C00468 KEGG Compound 12594 PubChem-compound UDP-GLUCURONATE BioCyc 6031 PubChem-compound 1010 ChemSpider HMDB00363 HMDB 1.0 8036443 ChemSpider 1.0 1.0 C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 HMDB01425 HMDB C02538 KEGG Compound HMDB00217 HMDB Testosterone CHEBI:17263 ChEBI C19H28O3 19-Hydroxytestosterone 304.20386 C19H30O2 5b-Dihydrotestosterone 290.22458 3001028 PubChem-compound CHEBI:5086 ChEBI Sulfotransferase family cytosolic 2B member 1 1.0 HMDB03959 HMDB 1180-25-2 CAS 17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O BioCyc HMDB00221 HMDB P08842 UniProt C00007 KEGG Compound C00006 KEGG Compound CHEBI:18009 ChEBI CHEBI:220467 ChEBI Dehydroepiandrosterone 50-28-2 CAS C00001 KEGG Compound Beta-D-Glucuronides BioCyc 1.0 P18405 UniProt C00005 KEGG Compound C00004 KEGG Compound SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O C00003 KEGG Compound CHEBI:16189 ChEBI NADP 1.0 Steryl-sulfatase UDP-glucuronosyltransferase 2B17 UDP-glucuronosyltransferase 2B11 Steroidogenesis SubPathway Oxygen Estrone sulfate C11134 KEGG Compound BiologicalState49 Homo sapiens, Cell, Endoplasmic Reticulum Membrane Cytochrome P450 19A1 C01227 KEGG Compound C21H28N7O14P2 NAD 664.11694 1.0 6128 PubChem-compound C00015 KEGG Compound 5660 ChemSpider NAD(P) BioCyc P37058 UniProt 10189 ChemSpider Dehydroepiandrosterone sulfate H Hydrogen Ion 1.007825 C19H24O3 19-Oxoandrost-4-ene-3,17-dione 300.17255 5898 ChemSpider HMDB03955 HMDB CHEBI:17252 ChEBI 6238 PubChem-compound O75310 UniProt 53-84-9 CAS O75795 UniProt 17a-Hydroxypregnenolone 1.0 17-beta-Estradiol-3-glucuronide 5b-Dihydrotestosterone 482-67-7 CAS 19-Hydroxyandrost-4-ene-3,17-dione P14060 UniProt http://identifiers.org/smpdb/SMP00130 SMPDB P14061 UniProt 1.14.14.14 false 1.14.14.14 19-Oxoandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → Estrone + Formic acid + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 19-Hydroxyandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → 19-Oxoandrost-4-ene-3,17-dione + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT CL:0000000 CELL TYPE ONTOLOGY 1.14.14.14 false 1.14.14.14 Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 Oxygen + Reduced flavoprotein + Testosterone → 19-Hydroxytestosterone + Oxidized flavoprotein + Water LEFT_TO_RIGHT Dihydrotestosterone 1.3.1.22 false 1.3.1.22 Dihydrotestosterone + NADP ↔ Hydrogen Ion + NADPH + Testosterone REVERSIBLE SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O SMILES C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O 17465008 ChemSpider 3-oxo-5-alpha-steroid 4-dehydrogenase 1 C00280 KEGG Compound 1.14.14.14 false 1.14.14.14 19-Oxotestosterone + Oxygen + Reduced flavoprotein → Estradiol + Formic acid + Oxidized flavoprotein LEFT_TO_RIGHT HMDB02961 HMDB 1.14.14.14 false 1.14.14.14 19-Hydroxytestosterone + Oxygen + Reduced flavoprotein → 19-Oxotestosterone + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT 1.1.1.62 false 1.1.1.62 Estradiol + NADP ↔ Estrone + NADPH REVERSIBLE 2.8.2.4 false 2.8.2.4 Estrone + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Estrone sulfate LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT C00167 KEGG Compound 108192 PubChem-compound 1.0 Estradiol 17-beta-dehydrogenase 1 17a-Hydroxypregnenolone SubPathwayOutput 12074 ChemSpider Testosterone 17-beta-dehydrogenase 3 C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 1.0 O00204 UniProt 3.1.6.2 false 3.1.6.2 Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Sulfate LEFT_TO_RIGHT C10H15N5O13P2S Phosphoadenosine phosphosulfate 506.98624 C05297 KEGG Compound 140102 ChemSpider CPD-352 BioCyc C05503 KEGG Compound 1.0 SMILES [O-]S([O-])(=O)=O C00054 KEGG Compound C00053 KEGG Compound 19-Hydroxyandrost-4-ene-3,17-dione 7732-18-5 CAS C00059 KEGG Compound C00058 KEGG Compound 1.0 19-Oxotestosterone 1.0 Water SMILES [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Estrogen sulfotransferase FORMATE BioCyc Oxidized flavoprotein 16522 ChemSpider Reaction24 false 17-Hydroxyprogesterone → Androstenedione LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Testosterone → Testosterone glucuronide LEFT_TO_RIGHT 68-96-2 CAS 1.3.1.3 false 1.3.1.3 5b-Dihydrotestosterone + NADP ↔ Hydrogen Ion + NADPH + Testosterone REVERSIBLE Estrogen sulfotransferase 1.0 C19H30O2 Dihydrotestosterone 290.22458 11302 PubChem-compound 10214 PubChem-compound Reaction21 false 17a-Hydroxypregnenolone → Dehydroepiandrosterone LEFT_TO_RIGHT BiologicalState18 Homo sapiens, Cell, Endoplasmic Reticulum SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 1.0 1.0 1.0 1.0 962 PubChem-compound 58-98-0 CAS 1.0 Reduced flavoprotein 1.0 C04555 KEGG Compound Oxidized flavoprotein SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 Steroid 17-alpha-hydroxylase/17,20 lyase C00080 KEGG Compound SMILES O=O BiologicalState8 Homo sapiens, Cell, Cytoplasm SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 5809 ChemSpider SMILES OC=O 1.0 1.0 Estradiol 17-beta-dehydrogenase 1 C01176 KEGG Compound 53-43-0 CAS Steryl-sulfatase Sulfotransferase family cytosolic 2B member 1 Testosterone 1.0 1.0 64-18-6 CAS 3-oxo-5-beta-steroid 4-dehydrogenase 16399653 PubChem-compound 22833512 PubChem-compound Androstenedione SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO UDP-glucuronosyltransferase 2B11 1.0 P49888 UniProt ReactionCatalysis929 ACTIVATION H2O Water 18.010565 1.0 Uridine 5'-diphosphate 18667985 ChemSpider NADH BioCyc Testosterone 17-beta-dehydrogenase 3 NAD BioCyc 977 PubChem-compound SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O Steroid 17-alpha-hydroxylase/17,20 lyase P51857 UniProt Formic acid UDP-glucuronosyltransferase 2B17 NAD Reduced flavoprotein 17215925 ChemSpider 97270 ChemSpider 2.0 O4S Sulfate 95.95173 19-Hydroxytestosterone SMILES O C19H28O2 Testosterone 288.20892 C21H30O3 17-Hydroxyprogesterone 330.21948 ReactionCatalysis27 ACTIVATION Cytochrome P450 19A1 2.8.2.2 false 2.8.2.2 Dehydroepiandrosterone + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfate LEFT_TO_RIGHT 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 2616-64-0 CAS ReactionCatalysis29 ACTIVATION C19H26O2 Androstenedione 286.19327 10635 PubChem-compound ReactionCatalysis20 ACTIVATION ReactionCatalysis24 ACTIVATION 6002 ChemSpider Reduced flavoprotein ReactionCatalysis22 ACTIVATION Uridine diphosphate glucuronic acid Water CHEBI:15846 ChEBI CHEBI:16814 ChEBI HMDB00935 HMDB C10H15N5O10P2 Adenosine 3',5'-diphosphate 427.02942 5870 PubChem-compound 53-59-8 CAS 10827 ChemSpider 651-48-9 CAS 1.0 ReactionCatalysis30 ACTIVATION 5757 PubChem-compound ESTRONE-SULFATE BioCyc 1038 PubChem-compound ReactionCatalysis34 ACTIVATION ReactionCatalysis35 ACTIVATION 16395893 PubChem-compound ReactionCatalysis32 ACTIVATION ReactionCatalysis33 ACTIVATION 17-Hydroxyprogesterone SubPathwayOutput 1.0 C24H32O8 17-beta-Estradiol-3-glucuronide 448.20972 278 ChemSpider C18H22O5S Estrone sulfate 350.1188 17461292 ChemSpider 13783824 PubChem-compound HMDB00902 HMDB CHEBI:16908 ChEBI ReactionCatalysis49 ACTIVATION Sulfate ReactionCatalysis47 ACTIVATION ReactionCatalysis48 ACTIVATION ReactionCatalysis46 ACTIVATION HMDB06224 HMDB 13628409 ChemSpider 221136 ChemSpider SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O HMDB03193 HMDB C21H30N7O17P3 NADPH 745.0911 3-5-ADP BioCyc C21H29N7O17P3 NADP 744.08325 C21H32O3 17a-Hydroxypregnenolone 332.23514 1.0 DEHYDRO-EPIANDROSTERONE-SULFATE BioCyc NADPH BioCyc 1053-73-2 CAS 1.0 CPD-6641 BioCyc ANDROST4ENE BioCyc 58-68-4 CAS 2126-37-6 CAS SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3 1.0 SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O C19H26O3 19-Hydroxyandrost-4-ene-3,17-dione 302.1882 1.0 1.0 510-64-5 CAS NADH Oxygen Androstenedione 1.0 Estrogen sulfotransferase C19H26O3 19-Oxotestosterone 302.1882 9799 ChemSpider 1.0 58-22-0 CAS C05138 KEGG Compound SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O SMILES [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C 1.0 SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O 159296 PubChem-compound 17473 PubChem-compound CHEBI:28835 ChEBI 91451 PubChem-compound Estrone Oxygen 53-57-6 CAS 17-Hydroxyprogesterone Reaction51 false Dehydroepiandrosterone + NAD → Androstenedione + Hydrogen Ion + NADH LEFT_TO_RIGHT HMDB06770 HMDB Reaction55 false 17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + Hydrogen Ion + NADH LEFT_TO_RIGHT C21H29N7O14P2 NADH 665.12476 1117 PubChem-compound 1.0 C19H28O2 Dehydroepiandrosterone 288.20892 1.0 571-22-2 CAS GO:0005737 GENE ONTOLOGY 1.0 Dehydroepiandrosterone CHEBI:17985 ChEBI 1.0 19-Oxoandrost-4-ene-3,17-dione Estradiol Endoplasmic Reticulum Endoplasmic Reticulum Membrane 1085 ChemSpider 4075-13-2 CAS NADH SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O C00951 KEGG Compound Androstenedione CHEBI:17980 ChEBI UDP BioCyc 5682 ChemSpider 521-18-6 CAS C05293 KEGG Compound C05295 KEGG Compound Reduced flavoprotein C05294 KEGG Compound C05290 KEGG Compound Dehydroepiandrosterone sulfate HMDB06769 HMDB CHEBI:16422 ChEBI HMDB06768 HMDB Estradiol SMILES [H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O 3-oxo-5-beta-steroid 4-dehydrogenase P05093 UniProt 5554 ChemSpider 5675 ChemSpider 5791 ChemSpider Water NAD 18971002 PubChem-compound Cytoplasm NADPH CHEBI:28750 ChEBI CHEBI:428206 ChEBI Cell NH42SO4 BioCyc 12850019 PubChem-compound 1.0 ESTRONE BioCyc CHEBI:36489 ChEBI 2.0 388299 ChemSpider 1.0 HMDB00077 HMDB C18H22O2 Estrone 270.162 Hydrogen Ion O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 9860744 PubChem-compound 19-Hydroxytestosterone GO:0005789 GENE ONTOLOGY C18H24O2 Estradiol 272.17764 GO:0005783 GENE ONTOLOGY 7782-44-7 CAS SMILES [H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C 9606 TAXONOMY 1.0 53-16-7 CAS 1.0 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O CHEBI:16330 ChEBI PW000141 PathWhiz HMDB00295 HMDB HMDB00053 HMDB 5893 PubChem-compound HMDB02111 HMDB PAPS BioCyc 1.0 CHEBI:30751 ChEBI http://identifiers.org/smpdb/SMP00068 SMPDB Oxidized flavoprotein CHEBI:15377 ChEBI Cytochrome P450 19A1 CHEBI:15379 ChEBI C03917 KEGG Compound CHEBI:15378 ChEBI SMILES [H+] CHEBI:16469 ChEBI